Gary Vaynerchuk, The People's Entrepreneur. Interviewed

Gary Vaynerchuk is arguably one of the most successful social entrepreneurs of our digital age. At 41 years old, he has done many things in his professional life that most will never accomplish. He aspires to buy the New York Jets one day, and I bet that goal will come true. He has legions of fanatics, followers and supporters that hang on his every word, tweet, post and vlog.

Often dressed in a hoodie and jeans, he is far from traditional in everything he does. His language, a bit rough around the edge does not reflect the soft edge compassionate and empathetic family man and partner Gary Vee really is. His client list from the full service digital agency he runs, VaynerMedia reads like a who's who of big time Fortune 500 companies. I had a few minutes with Gary as he called me from the road, between a fully packed schedule of meetings, calls and interviews. For the record, he was right on time:

Doug - Do you believe in people from the word “GO” or are you a prove it to me guy?

Gary - Normally from the word go if my intuition says go for it and I am more of a, you lose respect if you don’t do it. From me, you don’t have to earn it. I am much more comfortable and optimistic of where a person is and where they are going, so I am far more believing in people from the word go and then let them prove to me that I was wrong. The truth is I have lost and won that game many times. I think many people who are not optimistic have taken themselves out of potentially fruitful relationships, because they are picky and have too much ego. Who the hell are you, who the fuck are you, that the person has to prove it to you?

When I compete and am building businesses, I want to win, at all costs as long as it’s done the honorable way.

— Gary Vaynerchuk

Doug - Gary, has it been like that for you from the beginning or has it evolved over the years?

Gary - I think I am pulling from both sides. Whoever is the athlete of today, when he is on the court and he is the biggest killer when he is on the ice or the court or the field and then as soon as it’s over, will come and babysit your family, that’s who I am. I want to put everybody out of business. I want to win. But do I really want to put them out of business? Of course not, I don’t want people to have pain in real life. When I compete and am building businesses, I want to win, at all costs as long as it’s done the honorable way.

Doug - We all have tapes playing in our head and the tapes tell you to stay down, don’t even fucking try it. How do you stop the tapes from playing in your head?

Gary - You know what, I am a real practical guy. I don’t think it is practical for you to worry about what your parents or your girlfriend or the press or anonymous people are saying. I don’t think it is a smart way to run your life. I hear everybody but I listen to nobody. I respect everybody’s opinion but I just want to go down fighting for the shit that I believe in. I know who I am, I know what I believe in. I know my intent is good. So, (the word) "no" has been drowned out over the last 30 years through good old fashion focus on what I am good at.

I hear everybody but I listen to nobody. I respect everybody’s opinion but I just want to go down fighting for the shit that I believe in.

— Gary Vaynerchuk

Doug - We are raising kids in an everybody wins (and gets a trophy) environment, which is total bullshit. Can you comment about only giving trophies to first place but supporting the strengths of people even when they fuck up?

Gary - Fucking up is not the same as losing. I would call someone coming in second place as not good enough, but it’s not fucking up. To me, it’s very easy to give trophies only to the winner, while still supporting people. You put things into context. You’re not going to be the prettiest, the fastest, the strongest. You need to focus on what you are best at and do as much of that as possible, even if... look, being a businessman is the thing I decided I was going to be best at. I may not become the ultimate, most successful businessman of all time, but I am surely glad I decided to be a businessman versus a surfer or a cook or a mechanic because this is what comes natural to me and what I love the most.